Syntheses, crystal structures and inter­molecular inter­actions of six novel py­rimi­din-2-yl-substituted tri­aryl­tri­az­oles

Six new py­rimi­din-2-yl-substituted tri­aryl­tri­az­oles, namely, 4-(4-R-phen­yl)-3-(pyri­din-2-yl)-5-(py­rimi­din-2-yl)-1,2,4-tri­az­oles [L¹: R = meth­oxy (OCH₃); L²: R = methyl (CH₃); L³: R = nil (H); L⁴: R = bromo (Br); L⁵: R = chloro (Cl); L⁶: R = fluoro (F)] have been successfully synthesized with yields in the range 68.3–81.7%. Com­pounds L^1–6 have been characterized by UV–Vis, FT–IR, ¹H NMR and ESI–MS spectroscopy, and elemental analysis. In addition, the structures of L^2–6 and the ethanol mono­solvate of L² (L²·C₂H₅OH) have been determined by single-crystal X-ray dif­frac­tion. A combination of inter­molecular O—H...N, C—H...O, C—H...N and C—H...π hydrogen bonds connects the components of L²·C₂H₅OH into a three-dimensional (3D) framework. A combination of three inter­molecular C—H...N hydrogen bonds links the mol­ecules of L² or L³ into two dif­ferent 3D networks. Both L⁴ and L⁵ show a similar 3D net structure through two inter­molecular C—H...N hydrogen bonds and one kind of C—H...π inter­action. However, L⁶ displays a more complicated 3D net structure via three inter­molecular C—H...N hydrogen bonds and one kind of C—H...π inter­action. Notably, an inter­action between the π-electrons and the lone-pair p-electrons of a halogen atom (Br, Cl and F) is observed in L^4–6, which will further stabilize the 3D networks. The inter­molecular inter­actions in L²·C₂H₅OH and L^2–6 were further investigated by 3D Hirshfeld surface analyses and 2D fingerprint plots to show that the prominent inter­actions are H...H, N...H/H...N and C...H/H...C contacts.

Computing details

4-(4-Methylphenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole ethanol monosolvate (L2.C2H5OH)

Crystal data

C18H14N6·C2H6O	Z = 2
Mr = 360.42	F(000) = 380
Triclinic, P1	Dx = 1.277 Mg m^−3
a = 9.455 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.628 (8) Å	Cell parameters from 1462 reflections
c = 12.023 (10) Å	θ = 2.4–21.7°
α = 69.506 (10)°	µ = 0.08 mm^−1
β = 79.904 (12)°	T = 293 K
γ = 66.215 (11)°	Block, clear light colourless
V = 937.3 (13) Å^3	0.19 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD area detector diffractometer	2042 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
phi and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.984, Tmax = 0.991	k = −11→11
6792 measured reflections	l = −13→14
3305 independent reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.197	w = 1/[σ^2(Fo^2) + (0.1138P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3305 reflections	Δρmax = 0.54 e Å^−3
247 parameters	Δρmin = −0.31 e Å^−3
13 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.9353 (3)	0.2070 (3)	0.8372 (2)	0.0721 (8)
N2	0.8502 (3)	0.3247 (3)	0.5367 (2)	0.0565 (7)
N3	0.7357 (3)	0.3032 (3)	0.49514 (19)	0.0558 (7)
N4	0.6887 (2)	0.2718 (2)	0.68607 (17)	0.0424 (6)
N5	0.4824 (3)	0.1168 (3)	0.6702 (2)	0.0570 (7)
N6	0.4419 (3)	0.2999 (3)	0.4735 (2)	0.0604 (7)
C1	1.0356 (5)	0.2029 (5)	0.9042 (3)	0.0923 (13)
H1	1.047673	0.132340	0.981106	0.111*
C2	1.1231 (4)	0.2976 (5)	0.8658 (4)	0.0908 (12)
H2	1.192204	0.290709	0.915696	0.109*
C3	1.1062 (4)	0.4001 (4)	0.7547 (4)	0.0779 (10)
H3	1.163903	0.465035	0.726720	0.093*
C4	1.0038 (3)	0.4084 (4)	0.6830 (3)	0.0591 (8)
H4	0.990150	0.479194	0.606141	0.071*
C5	0.9216 (3)	0.3097 (3)	0.7270 (3)	0.0519 (7)
C6	0.8202 (3)	0.3051 (3)	0.6501 (2)	0.0465 (7)
C7	0.6405 (3)	0.2726 (3)	0.5852 (2)	0.0451 (7)
C8	0.5107 (3)	0.2293 (3)	0.5769 (2)	0.0454 (7)
C9	0.3336 (4)	0.2493 (4)	0.4644 (3)	0.0678 (9)
H9	0.282112	0.294333	0.393682	0.081*
C10	0.2944 (3)	0.1352 (4)	0.5532 (3)	0.0663 (9)
H10	0.218794	0.101512	0.544282	0.080*
C11	0.3715 (3)	0.0727 (4)	0.6558 (3)	0.0670 (9)
H11	0.345771	−0.003971	0.718614	0.080*
C12	0.5992 (3)	0.2806 (3)	0.7965 (2)	0.0409 (6)
C13	0.6242 (3)	0.1473 (4)	0.8948 (2)	0.0576 (8)
H13	0.694940	0.048344	0.890597	0.069*
C14	0.5430 (4)	0.1625 (4)	0.9996 (2)	0.0645 (9)
H14	0.559807	0.072510	1.066172	0.077*
C15	0.4374 (4)	0.3076 (4)	1.0082 (2)	0.0571 (8)
C16	0.4129 (3)	0.4379 (4)	0.9081 (3)	0.0585 (8)
H16	0.340327	0.536496	0.911420	0.070*
C17	0.4947 (3)	0.4252 (3)	0.8015 (2)	0.0496 (7)
H17	0.478021	0.514711	0.734484	0.060*
C18	0.3492 (5)	0.3233 (5)	1.1240 (3)	0.0936 (13)
H18A	0.295129	0.251033	1.151200	0.140*
H18B	0.276236	0.430790	1.111696	0.140*
H18C	0.420407	0.297986	1.182579	0.140*
O1	0.7849 (3)	0.1999 (4)	0.2878 (2)	0.0960 (8)
H1A	0.772421	0.235221	0.343189	0.144*
C19	1.0594 (5)	0.1292 (6)	0.3210 (5)	0.1319 (18)
H19A	1.157812	0.100920	0.279131	0.198*
H19B	1.059019	0.041673	0.390943	0.198*
H19C	1.041388	0.221420	0.343545	0.198*
C20	0.9376 (6)	0.1648 (7)	0.2443 (4)	0.1362 (19)
H20A	0.939953	0.254738	0.175537	0.163*
H20B	0.965645	0.074129	0.215827	0.163*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0834 (18)	0.086 (2)	0.0587 (16)	−0.0527 (16)	−0.0174 (14)	−0.0042 (15)
N2	0.0560 (14)	0.0713 (17)	0.0470 (14)	−0.0316 (13)	0.0061 (11)	−0.0184 (12)
N3	0.0571 (14)	0.0705 (17)	0.0421 (13)	−0.0289 (13)	0.0043 (11)	−0.0171 (12)
N4	0.0463 (12)	0.0467 (13)	0.0348 (11)	−0.0210 (10)	−0.0006 (9)	−0.0093 (10)
N5	0.0610 (14)	0.0710 (17)	0.0456 (14)	−0.0367 (13)	−0.0063 (11)	−0.0093 (12)
N6	0.0627 (15)	0.0678 (17)	0.0459 (14)	−0.0200 (13)	−0.0166 (12)	−0.0101 (12)
C1	0.107 (3)	0.120 (3)	0.070 (2)	−0.068 (3)	−0.032 (2)	−0.008 (2)
C2	0.078 (2)	0.112 (3)	0.107 (3)	−0.053 (2)	−0.020 (2)	−0.035 (3)
C3	0.064 (2)	0.076 (3)	0.110 (3)	−0.0412 (19)	−0.001 (2)	−0.031 (2)
C4	0.0516 (16)	0.0555 (19)	0.074 (2)	−0.0276 (15)	0.0051 (15)	−0.0186 (16)
C5	0.0457 (15)	0.0542 (18)	0.0591 (18)	−0.0208 (14)	0.0017 (13)	−0.0205 (15)
C6	0.0452 (15)	0.0500 (17)	0.0449 (16)	−0.0216 (13)	0.0024 (12)	−0.0127 (13)
C7	0.0491 (15)	0.0501 (17)	0.0362 (14)	−0.0192 (13)	0.0001 (12)	−0.0134 (12)
C8	0.0449 (14)	0.0528 (17)	0.0371 (14)	−0.0155 (13)	−0.0002 (11)	−0.0160 (13)
C9	0.0621 (19)	0.086 (3)	0.0533 (19)	−0.0206 (18)	−0.0179 (15)	−0.0197 (18)
C10	0.0542 (18)	0.089 (2)	0.069 (2)	−0.0317 (17)	−0.0082 (16)	−0.0312 (19)
C11	0.0652 (19)	0.085 (2)	0.0576 (19)	−0.0400 (18)	−0.0040 (15)	−0.0150 (17)
C12	0.0442 (14)	0.0494 (17)	0.0329 (13)	−0.0239 (13)	−0.0047 (11)	−0.0080 (12)
C13	0.0710 (19)	0.0512 (18)	0.0466 (17)	−0.0236 (15)	−0.0035 (14)	−0.0088 (14)
C14	0.090 (2)	0.073 (2)	0.0361 (16)	−0.047 (2)	0.0000 (15)	−0.0041 (15)
C15	0.0671 (19)	0.084 (2)	0.0418 (16)	−0.0509 (19)	0.0093 (14)	−0.0231 (16)
C16	0.0587 (17)	0.067 (2)	0.0561 (18)	−0.0283 (16)	0.0104 (14)	−0.0271 (16)
C17	0.0525 (16)	0.0537 (19)	0.0440 (16)	−0.0238 (15)	0.0003 (12)	−0.0129 (13)
C18	0.119 (3)	0.136 (4)	0.056 (2)	−0.079 (3)	0.034 (2)	−0.045 (2)
O1	0.0978 (19)	0.117 (2)	0.0848 (19)	−0.0393 (17)	0.0047 (15)	−0.0490 (17)
C19	0.104 (3)	0.131 (3)	0.149 (4)	−0.030 (3)	0.016 (3)	−0.056 (3)
C20	0.141 (4)	0.147 (4)	0.123 (3)	−0.027 (3)	0.010 (3)	−0.083 (3)

Geometric parameters (Å, º)

N1—C1	1.329 (4)	C10—C11	1.363 (4)
N1—C5	1.337 (4)	C11—H11	0.9300
N2—N3	1.381 (3)	C12—C13	1.375 (4)
N2—C6	1.304 (3)	C12—C17	1.359 (4)
N3—C7	1.311 (3)	C13—H13	0.9300
N4—C6	1.369 (3)	C13—C14	1.377 (4)
N4—C7	1.365 (3)	C14—H14	0.9300
N4—C12	1.453 (3)	C14—C15	1.379 (4)
N5—C8	1.334 (3)	C15—C16	1.372 (4)
N5—C11	1.335 (4)	C15—C18	1.515 (4)
N6—C8	1.329 (3)	C16—H16	0.9300
N6—C9	1.333 (4)	C16—C17	1.394 (4)
C1—H1	0.9300	C17—H17	0.9300
C1—C2	1.382 (5)	C18—H18A	0.9600
C2—H2	0.9300	C18—H18B	0.9600
C2—C3	1.345 (5)	C18—H18C	0.9600
C3—H3	0.9300	O1—H1A	0.8200
C3—C4	1.367 (5)	O1—C20	1.392 (5)
C4—H4	0.9300	C19—H19A	0.9600
C4—C5	1.373 (4)	C19—H19B	0.9600
C5—C6	1.467 (4)	C19—H19C	0.9600
C7—C8	1.475 (4)	C19—C20	1.458 (4)
C9—H9	0.9300	C20—H20A	0.9700
C9—C10	1.361 (4)	C20—H20B	0.9700
C10—H10	0.9300
C1—N1—C5	116.3 (3)	N5—C11—H11	118.5
C6—N2—N3	107.1 (2)	C10—C11—H11	118.5
C7—N3—N2	107.5 (2)	C13—C12—N4	120.8 (2)
C6—N4—C12	126.3 (2)	C17—C12—N4	118.2 (2)
C7—N4—C6	104.3 (2)	C17—C12—C13	120.9 (3)
C7—N4—C12	127.2 (2)	C12—C13—H13	120.5
C8—N5—C11	115.0 (2)	C12—C13—C14	119.0 (3)
C8—N6—C9	114.6 (3)	C14—C13—H13	120.5
N1—C1—H1	118.2	C13—C14—H14	119.2
N1—C1—C2	123.6 (4)	C13—C14—C15	121.7 (3)
C2—C1—H1	118.2	C15—C14—H14	119.2
C1—C2—H2	120.7	C14—C15—C18	121.3 (3)
C3—C2—C1	118.5 (3)	C16—C15—C14	118.0 (3)
C3—C2—H2	120.7	C16—C15—C18	120.7 (3)
C2—C3—H3	120.2	C15—C16—H16	119.4
C2—C3—C4	119.7 (3)	C15—C16—C17	121.2 (3)
C4—C3—H3	120.2	C17—C16—H16	119.4
C3—C4—H4	120.8	C12—C17—C16	119.3 (3)
C3—C4—C5	118.5 (3)	C12—C17—H17	120.4
C5—C4—H4	120.8	C16—C17—H17	120.4
N1—C5—C4	123.3 (3)	C15—C18—H18A	109.5
N1—C5—C6	116.3 (3)	C15—C18—H18B	109.5
C4—C5—C6	120.2 (3)	C15—C18—H18C	109.5
N2—C6—N4	110.8 (2)	H18A—C18—H18B	109.5
N2—C6—C5	123.2 (2)	H18A—C18—H18C	109.5
N4—C6—C5	125.9 (2)	H18B—C18—H18C	109.5
N3—C7—N4	110.3 (2)	C20—O1—H1A	109.5
N3—C7—C8	123.0 (2)	H19A—C19—H19B	109.5
N4—C7—C8	126.4 (2)	H19A—C19—H19C	109.5
N5—C8—C7	116.8 (2)	H19B—C19—H19C	109.5
N6—C8—N5	127.4 (3)	C20—C19—H19A	109.5
N6—C8—C7	115.6 (2)	C20—C19—H19B	109.5
N6—C9—H9	118.3	C20—C19—H19C	109.5
N6—C9—C10	123.5 (3)	O1—C20—C19	120.2 (4)
C10—C9—H9	118.3	O1—C20—H20A	107.3
C9—C10—H10	121.7	O1—C20—H20B	107.3
C9—C10—C11	116.6 (3)	C19—C20—H20A	107.3
C11—C10—H10	121.7	C19—C20—H20B	107.3
N5—C11—C10	122.9 (3)	H20A—C20—H20B	106.9
N1—C1—C2—C3	0.1 (6)	C6—N4—C12—C13	−94.6 (3)
N1—C5—C6—N2	−142.7 (3)	C6—N4—C12—C17	82.7 (3)
N1—C5—C6—N4	33.4 (4)	C7—N4—C6—N2	0.0 (3)
N2—N3—C7—N4	−0.5 (3)	C7—N4—C6—C5	−176.6 (3)
N2—N3—C7—C8	−174.6 (2)	C7—N4—C12—C13	104.9 (3)
N3—N2—C6—N4	−0.3 (3)	C7—N4—C12—C17	−77.8 (3)
N3—N2—C6—C5	176.4 (2)	C8—N5—C11—C10	1.2 (5)
N3—C7—C8—N5	140.8 (3)	C8—N6—C9—C10	0.3 (4)
N3—C7—C8—N6	−34.7 (4)	C9—N6—C8—N5	−0.4 (4)
N4—C7—C8—N5	−32.3 (4)	C9—N6—C8—C7	174.6 (2)
N4—C7—C8—N6	152.1 (3)	C9—C10—C11—N5	−1.2 (5)
N4—C12—C13—C14	176.4 (2)	C11—N5—C8—N6	−0.3 (4)
N4—C12—C17—C16	−177.0 (2)	C11—N5—C8—C7	−175.3 (2)
N6—C9—C10—C11	0.5 (5)	C12—N4—C6—N2	−164.1 (2)
C1—N1—C5—C4	−0.6 (5)	C12—N4—C6—C5	19.3 (4)
C1—N1—C5—C6	175.3 (3)	C12—N4—C7—N3	164.2 (2)
C1—C2—C3—C4	0.1 (6)	C12—N4—C7—C8	−21.9 (4)
C2—C3—C4—C5	−0.5 (5)	C12—C13—C14—C15	0.1 (4)
C3—C4—C5—N1	0.8 (5)	C13—C12—C17—C16	0.4 (4)
C3—C4—C5—C6	−174.9 (3)	C13—C14—C15—C16	1.1 (4)
C4—C5—C6—N2	33.3 (4)	C13—C14—C15—C18	−179.7 (3)
C4—C5—C6—N4	−150.5 (3)	C14—C15—C16—C17	−1.6 (4)
C5—N1—C1—C2	0.2 (6)	C15—C16—C17—C12	0.9 (4)
C6—N2—N3—C7	0.5 (3)	C17—C12—C13—C14	−0.8 (4)
C6—N4—C7—N3	0.3 (3)	C18—C15—C16—C17	179.2 (3)
C6—N4—C7—C8	174.2 (2)

4-Phenyl-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L3)

Crystal data

C17H12N6	Dx = 1.310 Mg m^−3
Mr = 300.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1290 reflections
a = 8.5626 (16) Å	θ = 2.2–16.6°
b = 18.701 (4) Å	µ = 0.08 mm^−1
c = 19.024 (4) Å	T = 293 K
V = 3046.3 (10) Å^3	Block, clear light colourless
Z = 8	0.17 × 0.14 × 0.11 mm
F(000) = 1248

Data collection

Bruker APEXII CCD area detector diffractometer	1346 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
phi and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
Tmin = 0.986, Tmax = 0.991	k = −22→22
20705 measured reflections	l = −22→22
2701 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0664P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.135	(Δ/σ)max < 0.001
S = 0.92	Δρmax = 0.19 e Å^−3
2701 reflections	Δρmin = −0.17 e Å^−3
209 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0045 (7)
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2611 (3)	0.63964 (12)	0.80798 (11)	0.0609 (6)
N2	0.3929 (3)	0.75741 (11)	0.67566 (12)	0.0654 (7)
N3	0.3770 (3)	0.74752 (12)	0.60376 (12)	0.0685 (7)
N4	0.3426 (2)	0.64382 (10)	0.65638 (10)	0.0469 (5)
N5	0.4212 (3)	0.59210 (13)	0.50840 (11)	0.0711 (7)
N6	0.2171 (3)	0.67474 (12)	0.48277 (13)	0.0679 (7)
C1	0.2554 (4)	0.63366 (17)	0.87791 (15)	0.0722 (9)
H1	0.183476	0.601986	0.897180	0.087*
C2	0.3495 (4)	0.67147 (18)	0.92307 (15)	0.0815 (9)
H2	0.341471	0.665512	0.971466	0.098*
C3	0.4558 (4)	0.71830 (17)	0.89478 (16)	0.0823 (9)
H3	0.521022	0.744796	0.923915	0.099*
C4	0.4648 (3)	0.72564 (14)	0.82340 (15)	0.0622 (7)
H4	0.535822	0.757127	0.803127	0.075*
C5	0.3672 (3)	0.68566 (13)	0.78268 (13)	0.0511 (7)
C6	0.3706 (3)	0.69515 (13)	0.70601 (14)	0.0515 (7)
C7	0.3485 (3)	0.67978 (14)	0.59342 (14)	0.0533 (7)
C8	0.3275 (3)	0.64661 (14)	0.52365 (14)	0.0547 (7)
C9	0.2008 (3)	0.64351 (18)	0.41862 (17)	0.0755 (9)
H9	0.126224	0.661370	0.387743	0.091*
C10	0.2900 (4)	0.58703 (18)	0.39810 (16)	0.0789 (9)
H10	0.277146	0.565705	0.354317	0.095*
C11	0.3995 (4)	0.56308 (17)	0.44497 (16)	0.0830 (10)
H11	0.461945	0.524606	0.431979	0.100*
C12	0.3166 (3)	0.56847 (13)	0.66557 (12)	0.0481 (6)
C13	0.1898 (3)	0.53672 (17)	0.63395 (15)	0.0664 (8)
H13	0.118539	0.563968	0.608585	0.080*
C14	0.1701 (4)	0.46387 (19)	0.64046 (19)	0.0875 (10)
H14	0.087278	0.441638	0.617643	0.105*
C15	0.2707 (5)	0.42387 (17)	0.67999 (19)	0.0864 (11)
H15	0.254380	0.374995	0.685170	0.104*
C16	0.3957 (4)	0.45597 (15)	0.71197 (15)	0.0709 (8)
H16	0.464375	0.428659	0.738702	0.085*
C17	0.4207 (3)	0.52890 (13)	0.70480 (13)	0.0538 (7)
H17	0.506161	0.550692	0.726071	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0576 (15)	0.0683 (15)	0.0567 (15)	−0.0007 (12)	0.0050 (12)	−0.0074 (12)
N2	0.0728 (17)	0.0475 (14)	0.0759 (17)	−0.0059 (12)	0.0065 (13)	−0.0048 (12)
N3	0.0804 (18)	0.0537 (15)	0.0715 (17)	0.0008 (13)	0.0105 (14)	0.0004 (12)
N4	0.0465 (13)	0.0436 (12)	0.0506 (13)	−0.0029 (10)	0.0025 (9)	−0.0021 (10)
N5	0.0746 (18)	0.0815 (18)	0.0571 (15)	0.0256 (14)	−0.0045 (13)	−0.0079 (13)
N6	0.0593 (16)	0.0728 (17)	0.0715 (17)	0.0032 (12)	0.0031 (13)	0.0074 (14)
C1	0.074 (2)	0.086 (2)	0.0561 (19)	0.0075 (17)	0.0065 (16)	−0.0054 (16)
C2	0.088 (3)	0.102 (3)	0.0541 (18)	0.0295 (17)	−0.0038 (16)	−0.0119 (16)
C3	0.071 (2)	0.095 (2)	0.0809 (15)	0.0189 (15)	−0.0160 (16)	−0.0311 (18)
C4	0.0452 (16)	0.0584 (16)	0.0831 (15)	0.0007 (14)	−0.0038 (14)	−0.0199 (15)
C5	0.0432 (16)	0.0506 (16)	0.0595 (16)	0.0049 (14)	−0.0008 (13)	−0.0107 (13)
C6	0.0464 (16)	0.0452 (16)	0.0628 (17)	−0.0034 (13)	0.0036 (13)	−0.0069 (14)
C7	0.0492 (17)	0.0521 (17)	0.0587 (17)	0.0058 (13)	0.0053 (13)	0.0045 (14)
C8	0.0521 (17)	0.0583 (17)	0.0537 (17)	0.0037 (15)	0.0046 (14)	0.0052 (14)
C9	0.064 (2)	0.090 (2)	0.073 (2)	−0.0006 (18)	−0.0077 (17)	0.0113 (18)
C10	0.075 (2)	0.105 (3)	0.0564 (19)	0.0201 (19)	−0.0064 (16)	−0.0113 (18)
C11	0.088 (2)	0.097 (2)	0.063 (2)	0.032 (2)	−0.0099 (19)	−0.0135 (18)
C12	0.0486 (16)	0.0479 (16)	0.0479 (15)	−0.0063 (13)	0.0044 (13)	−0.0027 (13)
C13	0.0558 (19)	0.071 (2)	0.0724 (19)	−0.0126 (16)	−0.0048 (15)	−0.0079 (15)
C14	0.083 (3)	0.072 (2)	0.108 (3)	−0.036 (2)	0.002 (2)	−0.019 (2)
C15	0.104 (3)	0.0479 (19)	0.107 (3)	−0.017 (2)	0.023 (2)	−0.0058 (19)
C16	0.081 (2)	0.0552 (19)	0.076 (2)	0.0013 (18)	0.0086 (18)	0.0041 (15)
C17	0.0573 (18)	0.0505 (16)	0.0537 (16)	−0.0038 (13)	0.0044 (14)	−0.0012 (13)

Geometric parameters (Å, º)

N1—C1	1.336 (3)	C4—C5	1.363 (3)
N1—C5	1.341 (3)	C5—C6	1.470 (3)
N2—N3	1.387 (3)	C7—C8	1.476 (3)
N2—C6	1.314 (3)	C9—H9	0.9300
N3—C7	1.305 (3)	C9—C10	1.360 (4)
N4—C6	1.368 (3)	C10—H10	0.9300
N4—C7	1.375 (3)	C10—C11	1.369 (4)
N4—C12	1.437 (3)	C11—H11	0.9300
N5—C8	1.329 (3)	C12—C13	1.376 (3)
N5—C11	1.336 (3)	C12—C17	1.378 (3)
N6—C8	1.332 (3)	C13—H13	0.9300
N6—C9	1.360 (3)	C13—C14	1.378 (4)
C1—H1	0.9300	C14—H14	0.9300
C1—C2	1.374 (4)	C14—C15	1.366 (5)
C2—H2	0.9300	C15—H15	0.9300
C2—C3	1.373 (4)	C15—C16	1.370 (4)
C3—H3	0.9300	C16—H16	0.9300
C3—C4	1.367 (4)	C16—C17	1.387 (3)
C4—H4	0.9300	C17—H17	0.9300
C1—N1—C5	115.8 (2)	N5—C8—C7	116.4 (2)
C6—N2—N3	107.5 (2)	N6—C8—C7	116.4 (2)
C7—N3—N2	107.3 (2)	N6—C9—H9	118.9
C6—N4—C7	104.6 (2)	N6—C9—C10	122.2 (3)
C6—N4—C12	129.2 (2)	C10—C9—H9	118.9
C7—N4—C12	126.2 (2)	C9—C10—H10	121.6
C8—N5—C11	115.1 (2)	C9—C10—C11	116.8 (3)
C8—N6—C9	115.3 (2)	C11—C10—H10	121.6
N1—C1—H1	118.0	N5—C11—C10	123.4 (3)
N1—C1—C2	123.9 (3)	N5—C11—H11	118.3
C2—C1—H1	118.0	C10—C11—H11	118.3
C1—C2—H2	120.9	C13—C12—N4	119.5 (2)
C3—C2—C1	118.2 (3)	C13—C12—C17	121.0 (2)
C3—C2—H2	120.9	C17—C12—N4	119.4 (2)
C2—C3—H3	120.3	C12—C13—H13	120.5
C4—C3—C2	119.4 (3)	C12—C13—C14	118.9 (3)
C4—C3—H3	120.3	C14—C13—H13	120.5
C3—C4—H4	120.8	C13—C14—H14	119.5
C5—C4—C3	118.3 (3)	C15—C14—C13	120.9 (3)
C5—C4—H4	120.8	C15—C14—H14	119.5
N1—C5—C4	124.3 (3)	C14—C15—H15	120.1
N1—C5—C6	116.5 (2)	C14—C15—C16	119.8 (3)
C4—C5—C6	119.1 (3)	C16—C15—H15	120.1
N2—C6—N4	110.1 (2)	C15—C16—H16	119.7
N2—C6—C5	123.1 (2)	C15—C16—C17	120.5 (3)
N4—C6—C5	126.7 (2)	C17—C16—H16	119.7
N3—C7—N4	110.5 (2)	C12—C17—C16	118.8 (3)
N3—C7—C8	124.5 (2)	C12—C17—H17	120.6
N4—C7—C8	125.0 (2)	C16—C17—H17	120.6
N5—C8—N6	127.1 (3)
N1—C1—C2—C3	0.0 (5)	C6—N4—C7—C8	179.0 (2)
N1—C5—C6—N2	140.9 (3)	C6—N4—C12—C13	129.8 (3)
N1—C5—C6—N4	−35.0 (4)	C6—N4—C12—C17	−51.5 (3)
N2—N3—C7—N4	0.8 (3)	C7—N4—C6—N2	−0.4 (3)
N2—N3—C7—C8	−178.5 (2)	C7—N4—C6—C5	175.8 (2)
N3—N2—C6—N4	1.0 (3)	C7—N4—C12—C13	−52.0 (3)
N3—N2—C6—C5	−175.5 (2)	C7—N4—C12—C17	126.7 (3)
N3—C7—C8—N5	124.0 (3)	C8—N5—C11—C10	0.3 (5)
N3—C7—C8—N6	−55.8 (4)	C8—N6—C9—C10	0.7 (4)
N4—C7—C8—N5	−55.2 (3)	C9—N6—C8—N5	−0.1 (4)
N4—C7—C8—N6	125.0 (3)	C9—N6—C8—C7	179.6 (2)
N4—C12—C13—C14	177.0 (2)	C9—C10—C11—N5	0.2 (5)
N4—C12—C17—C16	−178.7 (2)	C11—N5—C8—N6	−0.4 (4)
N6—C9—C10—C11	−0.7 (5)	C11—N5—C8—C7	179.9 (2)
C1—N1—C5—C4	−0.7 (4)	C12—N4—C6—N2	178.1 (2)
C1—N1—C5—C6	−177.5 (2)	C12—N4—C6—C5	−5.7 (4)
C1—C2—C3—C4	−0.2 (4)	C12—N4—C7—N3	−178.8 (2)
C2—C3—C4—C5	−0.1 (4)	C12—N4—C7—C8	0.5 (4)
C3—C4—C5—N1	0.6 (4)	C12—C13—C14—C15	2.7 (5)
C3—C4—C5—C6	177.4 (2)	C13—C12—C17—C16	0.0 (4)
C4—C5—C6—N2	−36.2 (4)	C13—C14—C15—C16	−2.0 (5)
C4—C5—C6—N4	148.0 (2)	C14—C15—C16—C17	0.3 (5)
C5—N1—C1—C2	0.4 (4)	C15—C16—C17—C12	0.7 (4)
C6—N2—N3—C7	−1.1 (3)	C17—C12—C13—C14	−1.7 (4)
C6—N4—C7—N3	−0.3 (3)

4-(4-Bromophenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L4)

Crystal data

C17H11BrN6	Z = 2
Mr = 379.23	F(000) = 380
Triclinic, P1	Dx = 1.574 Mg m^−3
a = 8.5510 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4214 (15) Å	Cell parameters from 2667 reflections
c = 11.5813 (18) Å	θ = 2.4–26.1°
α = 85.894 (2)°	µ = 2.58 mm^−1
β = 70.776 (2)°	T = 293 K
γ = 65.640 (2)°	Block, clear light colourless
V = 800.3 (2) Å^3	0.19 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD area detector diffractometer	2264 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
phi and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.619, Tmax = 0.734	k = −11→11
5827 measured reflections	l = −13→13
2813 independent reflections

Refinement

Refinement on F^2	42 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0343P)^2 + 0.7585P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2813 reflections	Δρmax = 0.73 e Å^−3
217 parameters	Δρmin = −0.53 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.27151 (5)	0.65581 (6)	0.58278 (4)	0.07508 (19)
N1	0.4324 (4)	0.9672 (3)	0.6896 (3)	0.0628 (8)
N2	0.2244 (3)	0.7508 (3)	0.8981 (3)	0.0520 (7)
N3	0.2992 (3)	0.5913 (3)	0.9065 (2)	0.0493 (7)
N4	0.5182 (3)	0.6601 (3)	0.7952 (2)	0.0352 (5)
N5	0.7600 (4)	0.3286 (3)	0.7388 (3)	0.0595 (8)
N6	0.5368 (4)	0.2789 (4)	0.9008 (3)	0.0597 (8)
C1	0.4071 (6)	1.1130 (5)	0.6604 (4)	0.0787 (13)
H1	0.479963	1.126790	0.584641	0.094*
C2	0.2789 (6)	1.2443 (5)	0.7363 (5)	0.0808 (13)
H2	0.266611	1.343748	0.712749	0.097*
C3	0.1713 (6)	1.2240 (5)	0.8460 (4)	0.0804 (13)
H3	0.081477	1.310378	0.898076	0.096*
C4	0.1950 (5)	1.0760 (4)	0.8804 (3)	0.0610 (10)
H4	0.123224	1.060289	0.955799	0.073*
C5	0.3291 (4)	0.9502 (4)	0.7993 (3)	0.0461 (8)
C6	0.3560 (4)	0.7900 (4)	0.8317 (3)	0.0418 (7)
C7	0.4746 (4)	0.5384 (4)	0.8451 (3)	0.0390 (7)
C8	0.5994 (4)	0.3724 (4)	0.8267 (3)	0.0400 (7)
C9	0.6466 (6)	0.1271 (5)	0.8801 (4)	0.0752 (12)
H9	0.606912	0.057322	0.928239	0.090*
C10	0.8138 (7)	0.0686 (4)	0.7920 (4)	0.0769 (12)
H10	0.887981	−0.037842	0.779115	0.092*
C11	0.8660 (6)	0.1761 (4)	0.7238 (4)	0.0768 (12)
H11	0.980552	0.141022	0.664281	0.092*
C12	0.6983 (3)	0.6579 (3)	0.7434 (3)	0.0337 (6)
C13	0.7943 (4)	0.6467 (3)	0.8207 (3)	0.0370 (6)
H13	0.744552	0.639134	0.904150	0.044*
C14	0.9656 (4)	0.6466 (3)	0.7735 (3)	0.0421 (7)
H14	1.032378	0.639405	0.824585	0.050*
C15	1.0353 (4)	0.6575 (4)	0.6491 (3)	0.0529 (6)
C16	0.9405 (4)	0.6665 (4)	0.5715 (3)	0.0459 (7)
H16	0.991259	0.671997	0.487854	0.055*
C17	0.7694 (4)	0.6673 (3)	0.6186 (3)	0.0407 (7)
H17	0.703110	0.674001	0.567279	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0427 (2)	0.1164 (4)	0.0665 (3)	−0.0476 (2)	0.00220 (17)	−0.0005 (2)
N1	0.0529 (17)	0.0464 (17)	0.0630 (19)	−0.0077 (13)	−0.0040 (15)	0.0056 (14)
N2	0.0300 (13)	0.0641 (19)	0.0564 (17)	−0.0192 (13)	−0.0065 (12)	−0.0007 (14)
N3	0.0376 (14)	0.0654 (19)	0.0476 (15)	−0.0287 (13)	−0.0075 (12)	0.0036 (13)
N4	0.0268 (11)	0.0404 (13)	0.0367 (13)	−0.0148 (10)	−0.0072 (10)	0.0034 (10)
N5	0.0580 (17)	0.0383 (16)	0.0620 (18)	−0.0166 (13)	0.0005 (14)	0.0050 (13)
N6	0.0668 (19)	0.0611 (19)	0.0567 (18)	−0.0386 (16)	−0.0140 (15)	0.0175 (14)
C1	0.071 (3)	0.052 (2)	0.081 (3)	−0.009 (2)	−0.008 (2)	0.018 (2)
C2	0.082 (3)	0.045 (2)	0.093 (3)	−0.008 (2)	−0.027 (3)	0.011 (2)
C3	0.071 (3)	0.054 (2)	0.084 (3)	0.004 (2)	−0.020 (2)	−0.013 (2)
C4	0.0468 (19)	0.058 (2)	0.056 (2)	−0.0051 (16)	−0.0084 (16)	−0.0042 (17)
C5	0.0298 (15)	0.0451 (18)	0.0528 (19)	−0.0064 (13)	−0.0116 (14)	−0.0010 (15)
C6	0.0269 (14)	0.0490 (18)	0.0427 (17)	−0.0117 (13)	−0.0066 (12)	−0.0049 (14)
C7	0.0361 (15)	0.0527 (18)	0.0346 (15)	−0.0258 (14)	−0.0106 (12)	0.0062 (13)
C8	0.0442 (16)	0.0481 (18)	0.0362 (16)	−0.0274 (14)	−0.0135 (13)	0.0055 (13)
C9	0.096 (3)	0.066 (3)	0.077 (3)	−0.051 (3)	−0.025 (3)	0.029 (2)
C10	0.102 (3)	0.041 (2)	0.080 (3)	−0.030 (2)	−0.022 (3)	0.0097 (19)
C11	0.076 (3)	0.049 (2)	0.073 (3)	−0.0188 (19)	0.007 (2)	0.0035 (19)
C12	0.0274 (12)	0.0310 (13)	0.0391 (14)	−0.0129 (10)	−0.0053 (11)	0.0021 (11)
C13	0.0326 (13)	0.0396 (14)	0.0348 (14)	−0.0160 (11)	−0.0049 (11)	0.0032 (11)
C14	0.0329 (13)	0.0486 (16)	0.0464 (16)	−0.0200 (12)	−0.0107 (12)	0.0016 (13)
C15	0.0381 (9)	0.0694 (10)	0.0577 (10)	−0.0385 (8)	−0.0017 (9)	−0.0003 (9)
C16	0.0404 (15)	0.0497 (16)	0.0393 (15)	−0.0206 (13)	−0.0002 (12)	0.0021 (13)
C17	0.0354 (14)	0.0467 (16)	0.0352 (14)	−0.0151 (12)	−0.0080 (11)	0.0019 (12)

Geometric parameters (Å, º)

Br1—C15	1.903 (3)	C4—H4	0.9300
N1—C1	1.336 (5)	C4—C5	1.389 (5)
N1—C5	1.330 (4)	C5—C6	1.471 (5)
N2—N3	1.380 (4)	C7—C8	1.466 (4)
N2—C6	1.314 (4)	C9—H9	0.9300
N3—C7	1.317 (4)	C9—C10	1.363 (6)
N4—C6	1.374 (4)	C10—H10	0.9300
N4—C7	1.381 (4)	C10—C11	1.369 (5)
N4—C12	1.448 (3)	C11—H11	0.9300
N5—C8	1.329 (4)	C12—C13	1.373 (4)
N5—C11	1.332 (5)	C12—C17	1.384 (4)
N6—C8	1.333 (4)	C13—H13	0.9300
N6—C9	1.333 (5)	C13—C14	1.385 (4)
C1—H1	0.9300	C14—H14	0.9300
C1—C2	1.381 (6)	C14—C15	1.381 (4)
C2—H2	0.9300	C15—C16	1.372 (5)
C2—C3	1.356 (6)	C16—H16	0.9300
C3—H3	0.9300	C16—C17	1.380 (4)
C3—C4	1.373 (6)	C17—H17	0.9300
C5—N1—C1	117.1 (3)	N5—C8—C7	118.4 (3)
C6—N2—N3	107.6 (2)	N6—C8—C7	115.4 (3)
C7—N3—N2	107.6 (2)	N6—C9—H9	118.2
C6—N4—C7	104.4 (2)	N6—C9—C10	123.5 (3)
C6—N4—C12	126.8 (2)	C10—C9—H9	118.2
C7—N4—C12	127.1 (2)	C9—C10—H10	122.0
C8—N5—C11	115.9 (3)	C9—C10—C11	116.0 (4)
C9—N6—C8	115.4 (3)	C11—C10—H10	122.0
N1—C1—H1	118.2	N5—C11—C10	123.0 (4)
N1—C1—C2	123.7 (4)	N5—C11—H11	118.5
C2—C1—H1	118.2	C10—C11—H11	118.5
C1—C2—H2	120.9	C13—C12—N4	118.5 (2)
C3—C2—C1	118.1 (4)	C13—C12—C17	121.6 (3)
C3—C2—H2	120.9	C17—C12—N4	119.9 (3)
C2—C3—H3	120.0	C12—C13—H13	120.2
C2—C3—C4	120.0 (4)	C12—C13—C14	119.6 (3)
C4—C3—H3	120.0	C14—C13—H13	120.2
C3—C4—H4	120.9	C13—C14—H14	120.7
C3—C4—C5	118.2 (4)	C15—C14—C13	118.6 (3)
C5—C4—H4	120.9	C15—C14—H14	120.7
N1—C5—C4	122.9 (3)	C14—C15—Br1	119.1 (3)
N1—C5—C6	117.2 (3)	C16—C15—Br1	119.1 (2)
C4—C5—C6	119.8 (3)	C16—C15—C14	121.8 (3)
N2—C6—N4	110.3 (3)	C15—C16—H16	120.2
N2—C6—C5	123.9 (3)	C15—C16—C17	119.6 (3)
N4—C6—C5	125.7 (3)	C17—C16—H16	120.2
N3—C7—N4	110.0 (3)	C12—C17—H17	120.6
N3—C7—C8	123.9 (3)	C16—C17—C12	118.8 (3)
N4—C7—C8	126.0 (2)	C16—C17—H17	120.6
N5—C8—N6	126.2 (3)
Br1—C15—C16—C17	179.8 (2)	C6—N4—C7—C8	176.2 (3)
N1—C1—C2—C3	−0.8 (8)	C6—N4—C12—C13	94.1 (3)
N1—C5—C6—N2	−144.9 (3)	C6—N4—C12—C17	−85.8 (4)
N1—C5—C6—N4	33.1 (5)	C7—N4—C6—N2	−0.2 (3)
N2—N3—C7—N4	−0.3 (3)	C7—N4—C6—C5	−178.4 (3)
N2—N3—C7—C8	−176.3 (3)	C7—N4—C12—C13	−69.0 (4)
N3—N2—C6—N4	0.0 (3)	C7—N4—C12—C17	111.1 (3)
N3—N2—C6—C5	178.3 (3)	C8—N5—C11—C10	1.4 (7)
N3—C7—C8—N5	162.8 (3)	C8—N6—C9—C10	1.6 (6)
N3—C7—C8—N6	−16.2 (4)	C9—N6—C8—N5	−2.1 (5)
N4—C7—C8—N5	−12.6 (5)	C9—N6—C8—C7	176.8 (3)
N4—C7—C8—N6	168.4 (3)	C9—C10—C11—N5	−1.7 (7)
N4—C12—C13—C14	−179.1 (2)	C11—N5—C8—N6	0.6 (5)
N4—C12—C17—C16	179.4 (3)	C11—N5—C8—C7	−178.2 (3)
N6—C9—C10—C11	0.1 (7)	C12—N4—C6—N2	−166.3 (3)
C1—N1—C5—C4	2.4 (6)	C12—N4—C6—C5	15.4 (5)
C1—N1—C5—C6	179.7 (3)	C12—N4—C7—N3	166.3 (3)
C1—C2—C3—C4	1.8 (7)	C12—N4—C7—C8	−17.8 (4)
C2—C3—C4—C5	−0.8 (7)	C12—C13—C14—C15	−0.2 (4)
C3—C4—C5—N1	−1.4 (6)	C13—C12—C17—C16	−0.5 (4)
C3—C4—C5—C6	−178.7 (3)	C13—C14—C15—Br1	−179.5 (2)
C4—C5—C6—N2	32.5 (5)	C13—C14—C15—C16	−0.7 (5)
C4—C5—C6—N4	−149.4 (3)	C14—C15—C16—C17	1.0 (5)
C5—N1—C1—C2	−1.3 (7)	C15—C16—C17—C12	−0.4 (4)
C6—N2—N3—C7	0.2 (3)	C17—C12—C13—C14	0.8 (4)
C6—N4—C7—N3	0.3 (3)

4-(4-Chlorophenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L5)

Crystal data

C17H11ClN6	Z = 2
Mr = 334.77	F(000) = 344
Triclinic, P1	Dx = 1.407 Mg m^−3
a = 8.5105 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3681 (14) Å	Cell parameters from 3029 reflections
c = 10.8959 (16) Å	θ = 2.6–26.5°
α = 81.355 (2)°	µ = 0.25 mm^−1
β = 82.482 (2)°	T = 293 K
γ = 67.388 (2)°	Block, clear light colourless
V = 790.3 (2) Å^3	0.18 × 0.17 × 0.14 mm

Data collection

Bruker APEXII CCD area detector diffractometer	2383 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
phi and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
Tmin = 0.955, Tmax = 0.965	k = −11→11
5712 measured reflections	l = −12→12
2765 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.253P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2765 reflections	Δρmax = 0.17 e Å^−3
217 parameters	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.00724 (6)	0.66378 (7)	0.40056 (5)	0.06079 (19)
N1	0.2531 (2)	0.9522 (2)	0.30700 (17)	0.0638 (5)
N2	0.17141 (19)	0.7360 (2)	0.09767 (15)	0.0519 (4)
N3	0.2479 (2)	0.5775 (2)	0.09445 (15)	0.0522 (4)
N4	0.39452 (17)	0.64924 (16)	0.20889 (13)	0.0376 (3)
N5	0.5750 (3)	0.3255 (2)	0.29005 (17)	0.0646 (5)
N6	0.4922 (3)	0.2676 (2)	0.10816 (17)	0.0665 (5)
C1	0.2042 (4)	1.0970 (3)	0.3366 (2)	0.0814 (8)
H1	0.232181	1.110408	0.412588	0.098*
C2	0.1149 (3)	1.2277 (3)	0.2616 (3)	0.0796 (7)
H2	0.083816	1.326243	0.286470	0.096*
C3	0.0735 (3)	1.2096 (3)	0.1510 (2)	0.0765 (7)
H3	0.012383	1.295962	0.098710	0.092*
C4	0.1226 (3)	1.0620 (3)	0.1161 (2)	0.0616 (6)
H4	0.096085	1.047237	0.040053	0.074*
C5	0.2118 (2)	0.9370 (2)	0.19654 (18)	0.0463 (4)
C6	0.2602 (2)	0.7767 (2)	0.16599 (16)	0.0421 (4)
C7	0.3809 (2)	0.5276 (2)	0.16051 (16)	0.0416 (4)
C8	0.4915 (2)	0.3633 (2)	0.18782 (17)	0.0456 (4)
C9	0.5897 (4)	0.1186 (3)	0.1370 (3)	0.0863 (8)
H9	0.593537	0.046315	0.085612	0.104*
C10	0.6844 (4)	0.0668 (3)	0.2380 (3)	0.0933 (9)
H10	0.753036	−0.037510	0.254984	0.112*
C11	0.6733 (4)	0.1761 (3)	0.3136 (3)	0.0886 (8)
H11	0.736249	0.144766	0.383099	0.106*
C12	0.5441 (2)	0.64901 (18)	0.25914 (15)	0.0352 (4)
C13	0.5468 (2)	0.6525 (2)	0.38479 (16)	0.0423 (4)
H13	0.452750	0.653274	0.439250	0.051*
C14	0.6907 (2)	0.6547 (2)	0.42902 (16)	0.0445 (4)
H14	0.694864	0.657181	0.513504	0.053*
C15	0.8283 (2)	0.6531 (2)	0.34571 (16)	0.0400 (4)
C16	0.8273 (2)	0.6466 (2)	0.22091 (17)	0.0443 (4)
H16	0.922184	0.643682	0.166676	0.053*
C17	0.6831 (2)	0.6444 (2)	0.17696 (16)	0.0417 (4)
H17	0.679923	0.639756	0.092688	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0501 (3)	0.0850 (4)	0.0577 (3)	−0.0339 (3)	−0.0209 (2)	−0.0005 (3)
N1	0.0710 (12)	0.0497 (10)	0.0616 (11)	−0.0055 (9)	−0.0249 (9)	−0.0084 (8)
N2	0.0412 (9)	0.0643 (11)	0.0537 (10)	−0.0217 (8)	−0.0122 (7)	−0.0042 (8)
N3	0.0477 (9)	0.0712 (11)	0.0504 (9)	−0.0333 (8)	−0.0080 (7)	−0.0105 (8)
N4	0.0330 (7)	0.0431 (8)	0.0391 (8)	−0.0156 (6)	−0.0055 (6)	−0.0058 (6)
N5	0.0837 (13)	0.0436 (10)	0.0632 (11)	−0.0177 (9)	−0.0148 (10)	−0.0045 (8)
N6	0.0839 (13)	0.0626 (12)	0.0634 (11)	−0.0359 (10)	0.0041 (10)	−0.0232 (9)
C1	0.101 (2)	0.0564 (14)	0.0742 (16)	−0.0038 (13)	−0.0302 (14)	−0.0179 (12)
C2	0.0843 (18)	0.0530 (14)	0.0854 (18)	−0.0039 (12)	−0.0153 (14)	−0.0110 (12)
C3	0.0712 (15)	0.0574 (14)	0.0769 (17)	−0.0002 (12)	−0.0149 (13)	0.0074 (12)
C4	0.0539 (12)	0.0676 (14)	0.0529 (12)	−0.0102 (10)	−0.0164 (10)	0.0012 (10)
C5	0.0352 (9)	0.0501 (11)	0.0493 (10)	−0.0111 (8)	−0.0067 (8)	−0.0027 (8)
C6	0.0325 (9)	0.0534 (11)	0.0397 (9)	−0.0158 (8)	−0.0072 (7)	−0.0001 (8)
C7	0.0412 (9)	0.0513 (10)	0.0400 (9)	−0.0250 (8)	−0.0001 (7)	−0.0093 (8)
C8	0.0509 (11)	0.0507 (11)	0.0430 (10)	−0.0284 (9)	0.0046 (8)	−0.0101 (8)
C9	0.118 (2)	0.0662 (17)	0.0839 (19)	−0.0437 (16)	0.0127 (17)	−0.0289 (14)
C10	0.118 (2)	0.0407 (13)	0.105 (2)	−0.0171 (14)	0.0076 (19)	−0.0079 (13)
C11	0.116 (2)	0.0506 (14)	0.0872 (19)	−0.0173 (14)	−0.0232 (17)	0.0028 (13)
C12	0.0320 (8)	0.0336 (8)	0.0405 (9)	−0.0113 (7)	−0.0085 (7)	−0.0036 (7)
C13	0.0377 (9)	0.0495 (10)	0.0382 (9)	−0.0156 (8)	−0.0020 (7)	−0.0032 (7)
C14	0.0460 (10)	0.0522 (11)	0.0355 (9)	−0.0168 (8)	−0.0110 (8)	−0.0025 (8)
C15	0.0355 (9)	0.0394 (9)	0.0462 (10)	−0.0126 (7)	−0.0157 (7)	−0.0008 (7)
C16	0.0355 (9)	0.0541 (11)	0.0447 (10)	−0.0182 (8)	−0.0025 (7)	−0.0058 (8)
C17	0.0406 (9)	0.0512 (10)	0.0357 (9)	−0.0180 (8)	−0.0051 (7)	−0.0080 (7)

Geometric parameters (Å, º)

Cl1—C15	1.7495 (16)	C4—H4	0.9300
N1—C1	1.334 (3)	C4—C5	1.377 (3)
N1—C5	1.339 (3)	C5—C6	1.475 (3)
N2—N3	1.377 (2)	C7—C8	1.471 (3)
N2—C6	1.313 (2)	C9—H9	0.9300
N3—C7	1.313 (2)	C9—C10	1.367 (4)
N4—C6	1.368 (2)	C10—H10	0.9300
N4—C7	1.374 (2)	C10—C11	1.377 (4)
N4—C12	1.449 (2)	C11—H11	0.9300
N5—C8	1.329 (3)	C12—C13	1.378 (2)
N5—C11	1.331 (3)	C12—C17	1.377 (2)
N6—C8	1.336 (2)	C13—H13	0.9300
N6—C9	1.335 (3)	C13—C14	1.382 (2)
C1—H1	0.9300	C14—H14	0.9300
C1—C2	1.374 (3)	C14—C15	1.381 (3)
C2—H2	0.9300	C15—C16	1.372 (3)
C2—C3	1.351 (4)	C16—H16	0.9300
C3—H3	0.9300	C16—C17	1.383 (2)
C3—C4	1.379 (3)	C17—H17	0.9300
C1—N1—C5	116.48 (18)	N5—C8—C7	116.99 (16)
C6—N2—N3	107.51 (15)	N6—C8—C7	115.71 (18)
C7—N3—N2	107.42 (14)	N6—C9—H9	118.3
C6—N4—C7	104.27 (14)	N6—C9—C10	123.4 (2)
C6—N4—C12	126.84 (14)	C10—C9—H9	118.3
C7—N4—C12	126.36 (14)	C9—C10—H10	121.6
C8—N5—C11	116.1 (2)	C9—C10—C11	116.9 (2)
C9—N6—C8	114.5 (2)	C11—C10—H10	121.6
N1—C1—H1	118.0	N5—C11—C10	121.9 (3)
N1—C1—C2	124.1 (2)	N5—C11—H11	119.1
C2—C1—H1	118.0	C10—C11—H11	119.1
C1—C2—H2	120.8	C13—C12—N4	120.92 (15)
C3—C2—C1	118.5 (2)	C17—C12—N4	117.61 (14)
C3—C2—H2	120.8	C17—C12—C13	121.47 (15)
C2—C3—H3	120.3	C12—C13—H13	120.4
C2—C3—C4	119.5 (2)	C12—C13—C14	119.27 (16)
C4—C3—H3	120.3	C14—C13—H13	120.4
C3—C4—H4	120.7	C13—C14—H14	120.5
C5—C4—C3	118.5 (2)	C15—C14—C13	118.92 (16)
C5—C4—H4	120.7	C15—C14—H14	120.5
N1—C5—C4	123.01 (19)	C14—C15—Cl1	119.00 (13)
N1—C5—C6	116.42 (16)	C16—C15—Cl1	119.04 (14)
C4—C5—C6	120.52 (18)	C16—C15—C14	121.95 (15)
N2—C6—N4	110.45 (16)	C15—C16—H16	120.5
N2—C6—C5	123.32 (16)	C15—C16—C17	118.96 (16)
N4—C6—C5	126.13 (15)	C17—C16—H16	120.5
N3—C7—N4	110.34 (16)	C12—C17—C16	119.40 (16)
N3—C7—C8	124.94 (16)	C12—C17—H17	120.3
N4—C7—C8	124.54 (15)	C16—C17—H17	120.3
N5—C8—N6	127.27 (19)
Cl1—C15—C16—C17	−177.46 (14)	C6—N4—C7—C8	−175.78 (16)
N1—C1—C2—C3	0.0 (5)	C6—N4—C12—C13	90.6 (2)
N1—C5—C6—N2	148.07 (19)	C6—N4—C12—C17	−89.8 (2)
N1—C5—C6—N4	−27.9 (3)	C7—N4—C6—N2	0.35 (19)
N2—N3—C7—N4	0.5 (2)	C7—N4—C6—C5	176.74 (16)
N2—N3—C7—C8	175.73 (15)	C7—N4—C12—C13	−110.35 (19)
N3—N2—C6—N4	−0.1 (2)	C7—N4—C12—C17	69.3 (2)
N3—N2—C6—C5	−176.59 (16)	C8—N5—C11—C10	−1.5 (4)
N3—C7—C8—N5	−154.66 (19)	C8—N6—C9—C10	−1.1 (4)
N3—C7—C8—N6	23.3 (3)	C9—N6—C8—N5	−0.5 (3)
N4—C7—C8—N5	19.9 (3)	C9—N6—C8—C7	−178.21 (19)
N4—C7—C8—N6	−162.08 (17)	C9—C10—C11—N5	0.1 (5)
N4—C12—C13—C14	−178.95 (16)	C11—N5—C8—N6	1.8 (3)
N4—C12—C17—C16	178.94 (15)	C11—N5—C8—C7	179.5 (2)
N6—C9—C10—C11	1.3 (5)	C12—N4—C6—N2	163.09 (15)
C1—N1—C5—C4	−0.5 (3)	C12—N4—C6—C5	−20.5 (3)
C1—N1—C5—C6	−177.8 (2)	C12—N4—C7—N3	−163.36 (16)
C1—C2—C3—C4	−0.5 (4)	C12—N4—C7—C8	21.4 (3)
C2—C3—C4—C5	0.5 (4)	C12—C13—C14—C15	−0.1 (3)
C3—C4—C5—N1	0.0 (3)	C13—C12—C17—C16	−1.4 (3)
C3—C4—C5—C6	177.2 (2)	C13—C14—C15—Cl1	177.46 (13)
C4—C5—C6—N2	−29.4 (3)	C13—C14—C15—C16	−1.2 (3)
C4—C5—C6—N4	154.69 (18)	C14—C15—C16—C17	1.2 (3)
C5—N1—C1—C2	0.5 (4)	C15—C16—C17—C12	0.1 (3)
C6—N2—N3—C7	−0.3 (2)	C17—C12—C13—C14	1.4 (3)
C6—N4—C7—N3	−0.51 (19)

4-(4-Fluorophenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L6)

Crystal data

C17H11FN6	Z = 2
Mr = 318.32	F(000) = 328
Triclinic, P1	Dx = 1.386 Mg m^−3
a = 8.624 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.503 (2) Å	Cell parameters from 1265 reflections
c = 10.471 (3) Å	θ = 2.4–22.0°
α = 80.312 (3)°	µ = 0.10 mm^−1
β = 81.512 (4)°	T = 293 K
γ = 64.780 (3)°	Block, clear light colourless
V = 762.5 (3) Å^3	0.18 × 0.14 × 0.12 mm

Data collection

Bruker APEXII CCD area detector diffractometer	1778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
phi and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.984, Tmax = 0.988	k = −11→11
5556 measured reflections	l = −12→12
2676 independent reflections

Refinement

Refinement on F^2	13 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0684P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2676 reflections	Δρmax = 0.19 e Å^−3
217 parameters	Δρmin = −0.23 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.97294 (17)	0.63947 (18)	0.39616 (14)	0.0802 (5)
N1	0.2472 (3)	0.9553 (2)	0.3243 (2)	0.0768 (7)
N2	0.1623 (2)	0.7479 (2)	0.11258 (19)	0.0584 (5)
N3	0.2434 (2)	0.5876 (2)	0.10485 (18)	0.0557 (5)
N4	0.39664 (19)	0.65217 (19)	0.21641 (15)	0.0406 (4)
N5	0.5977 (3)	0.3235 (2)	0.28799 (18)	0.0611 (6)
N6	0.4896 (3)	0.2738 (2)	0.1124 (2)	0.0671 (6)
C1	0.1997 (4)	1.1000 (3)	0.3536 (3)	0.0963 (11)
H1	0.226224	1.111040	0.433238	0.116*
C2	0.1144 (4)	1.2333 (3)	0.2740 (3)	0.0868 (9)
H2	0.086100	1.331697	0.298227	0.104*
C3	0.0725 (4)	1.2181 (3)	0.1592 (3)	0.0786 (9)
H3	0.011934	1.306441	0.103914	0.094*
C4	0.1202 (3)	1.0709 (3)	0.1249 (2)	0.0642 (7)
H4	0.094069	1.058242	0.045685	0.077*
C5	0.2070 (3)	0.9428 (3)	0.2098 (2)	0.0511 (6)
C6	0.2547 (3)	0.7834 (3)	0.1791 (2)	0.0473 (6)
C7	0.3832 (3)	0.5337 (2)	0.16723 (19)	0.0425 (5)
C8	0.4998 (3)	0.3667 (3)	0.1904 (2)	0.0452 (5)
C9	0.5904 (4)	0.1226 (4)	0.1394 (3)	0.0834 (9)
H9	0.587265	0.052364	0.088908	0.100*
C10	0.6978 (4)	0.0647 (3)	0.2366 (3)	0.0834 (9)
H10	0.767361	−0.041583	0.252592	0.100*
C11	0.6978 (4)	0.1712 (3)	0.3093 (3)	0.0785 (8)
H11	0.770398	0.136136	0.376134	0.094*
C12	0.5457 (2)	0.6483 (2)	0.26658 (19)	0.0398 (5)
C13	0.5525 (3)	0.6463 (2)	0.3963 (2)	0.0481 (6)
H13	0.459390	0.648340	0.454678	0.058*
C14	0.6985 (3)	0.6414 (3)	0.4407 (2)	0.0543 (6)
H14	0.705748	0.638370	0.528956	0.065*
C15	0.8314 (3)	0.6410 (3)	0.3519 (2)	0.0516 (6)
C16	0.8291 (3)	0.6428 (3)	0.2218 (2)	0.0517 (6)
H16	0.923012	0.641668	0.164667	0.062*
C17	0.6847 (3)	0.6465 (2)	0.1761 (2)	0.0468 (5)
H17	0.679518	0.647686	0.087790	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0649 (10)	0.1008 (12)	0.0907 (11)	−0.0423 (9)	−0.0384 (8)	−0.0028 (9)
N1	0.0919 (17)	0.0484 (13)	0.0765 (15)	−0.0051 (11)	−0.0370 (13)	−0.0119 (11)
N2	0.0472 (11)	0.0606 (13)	0.0704 (13)	−0.0209 (10)	−0.0193 (10)	−0.0063 (10)
N3	0.0498 (12)	0.0662 (14)	0.0604 (12)	−0.0296 (10)	−0.0129 (9)	−0.0090 (10)
N4	0.0365 (10)	0.0415 (10)	0.0446 (10)	−0.0143 (8)	−0.0090 (8)	−0.0075 (8)
N5	0.0760 (14)	0.0442 (12)	0.0597 (12)	−0.0170 (11)	−0.0186 (11)	−0.0074 (9)
N6	0.0852 (16)	0.0583 (14)	0.0668 (14)	−0.0333 (13)	−0.0060 (11)	−0.0210 (11)
C1	0.124 (3)	0.0550 (18)	0.090 (2)	−0.0032 (17)	−0.0455 (19)	−0.0194 (16)
C2	0.099 (2)	0.0508 (17)	0.094 (2)	−0.0072 (15)	−0.0263 (18)	−0.0134 (16)
C3	0.077 (2)	0.0538 (17)	0.0804 (19)	−0.0037 (15)	−0.0175 (16)	0.0021 (14)
C4	0.0564 (15)	0.0623 (17)	0.0613 (15)	−0.0110 (13)	−0.0156 (12)	−0.0024 (13)
C5	0.0399 (12)	0.0487 (14)	0.0577 (14)	−0.0099 (10)	−0.0091 (10)	−0.0066 (11)
C6	0.0372 (12)	0.0534 (14)	0.0502 (13)	−0.0164 (11)	−0.0103 (10)	−0.0038 (11)
C7	0.0419 (12)	0.0511 (13)	0.0406 (12)	−0.0241 (10)	−0.0022 (9)	−0.0089 (10)
C8	0.0481 (13)	0.0528 (14)	0.0431 (12)	−0.0288 (11)	0.0037 (10)	−0.0126 (10)
C9	0.112 (2)	0.065 (2)	0.084 (2)	−0.0427 (18)	0.0028 (18)	−0.0306 (16)
C10	0.107 (2)	0.0426 (15)	0.089 (2)	−0.0205 (15)	−0.0019 (18)	−0.0112 (15)
C11	0.094 (2)	0.0514 (17)	0.0813 (19)	−0.0182 (15)	−0.0244 (16)	−0.0023 (14)
C12	0.0365 (11)	0.0365 (11)	0.0478 (12)	−0.0131 (9)	−0.0136 (9)	−0.0053 (9)
C13	0.0475 (13)	0.0528 (14)	0.0445 (13)	−0.0203 (11)	−0.0068 (10)	−0.0054 (10)
C14	0.0628 (16)	0.0577 (15)	0.0466 (13)	−0.0251 (12)	−0.0206 (12)	−0.0024 (11)
C15	0.0455 (13)	0.0473 (13)	0.0678 (16)	−0.0195 (11)	−0.0264 (12)	−0.0025 (11)
C16	0.0398 (12)	0.0593 (15)	0.0590 (14)	−0.0222 (11)	−0.0065 (10)	−0.0081 (11)
C17	0.0440 (12)	0.0508 (13)	0.0479 (13)	−0.0193 (11)	−0.0097 (10)	−0.0076 (10)

Geometric parameters (Å, º)

F1—C15	1.362 (2)	C4—H4	0.9300
N1—C1	1.334 (3)	C4—C5	1.374 (3)
N1—C5	1.333 (3)	C5—C6	1.470 (3)
N2—N3	1.390 (3)	C7—C8	1.474 (3)
N2—C6	1.306 (3)	C9—H9	0.9300
N3—C7	1.317 (2)	C9—C10	1.360 (4)
N4—C6	1.372 (2)	C10—H10	0.9300
N4—C7	1.368 (2)	C10—C11	1.365 (4)
N4—C12	1.443 (2)	C11—H11	0.9300
N5—C8	1.320 (3)	C12—C13	1.365 (3)
N5—C11	1.332 (3)	C12—C17	1.410 (3)
N6—C8	1.335 (3)	C13—H13	0.9300
N6—C9	1.331 (4)	C13—C14	1.385 (3)
C1—H1	0.9300	C14—H14	0.9300
C1—C2	1.368 (4)	C14—C15	1.365 (3)
C2—H2	0.9300	C15—C16	1.362 (3)
C2—C3	1.352 (4)	C16—H16	0.9300
C3—H3	0.9300	C16—C17	1.384 (3)
C3—C4	1.375 (4)	C17—H17	0.9300
C5—N1—C1	116.7 (2)	N5—C8—C7	117.32 (18)
C6—N2—N3	107.64 (17)	N6—C8—C7	115.7 (2)
C7—N3—N2	106.77 (17)	N6—C9—H9	118.1
C6—N4—C12	126.52 (17)	N6—C9—C10	123.9 (3)
C7—N4—C6	104.51 (16)	C10—C9—H9	118.1
C7—N4—C12	127.31 (17)	C9—C10—H10	121.8
C8—N5—C11	116.1 (2)	C9—C10—C11	116.4 (3)
C9—N6—C8	114.4 (2)	C11—C10—H10	121.8
N1—C1—H1	117.9	N5—C11—C10	122.3 (3)
N1—C1—C2	124.2 (3)	N5—C11—H11	118.8
C2—C1—H1	117.9	C10—C11—H11	118.8
C1—C2—H2	120.9	C13—C12—N4	121.55 (18)
C3—C2—C1	118.2 (3)	C13—C12—C17	121.15 (18)
C3—C2—H2	120.9	C17—C12—N4	117.29 (17)
C2—C3—H3	120.3	C12—C13—H13	120.1
C2—C3—C4	119.4 (3)	C12—C13—C14	119.8 (2)
C4—C3—H3	120.3	C14—C13—H13	120.1
C3—C4—H4	120.6	C13—C14—H14	120.8
C5—C4—C3	118.8 (2)	C15—C14—C13	118.4 (2)
C5—C4—H4	120.6	C15—C14—H14	120.8
N1—C5—C4	122.7 (2)	F1—C15—C14	118.0 (2)
N1—C5—C6	116.71 (19)	F1—C15—C16	118.6 (2)
C4—C5—C6	120.6 (2)	C16—C15—C14	123.40 (19)
N2—C6—N4	110.47 (19)	C15—C16—H16	120.6
N2—C6—C5	123.29 (19)	C15—C16—C17	118.9 (2)
N4—C6—C5	126.23 (18)	C17—C16—H16	120.6
N3—C7—N4	110.62 (19)	C12—C17—H17	120.8
N3—C7—C8	124.28 (19)	C16—C17—C12	118.39 (19)
N4—C7—C8	124.89 (18)	C16—C17—H17	120.8
N5—C8—N6	126.9 (2)
F1—C15—C16—C17	−179.15 (19)	C6—N4—C7—C8	−175.15 (19)
N1—C1—C2—C3	1.3 (5)	C6—N4—C12—C13	88.4 (3)
N1—C5—C6—N2	145.4 (2)	C6—N4—C12—C17	−91.7 (3)
N1—C5—C6—N4	−33.3 (3)	C7—N4—C6—N2	0.0 (2)
N2—N3—C7—N4	0.4 (2)	C7—N4—C6—C5	178.8 (2)
N2—N3—C7—C8	175.31 (18)	C7—N4—C12—C13	−108.6 (2)
N3—N2—C6—N4	0.2 (2)	C7—N4—C12—C17	71.3 (3)
N3—N2—C6—C5	−178.7 (2)	C8—N5—C11—C10	−1.2 (4)
N3—C7—C8—N5	−157.6 (2)	C8—N6—C9—C10	−0.9 (4)
N3—C7—C8—N6	19.9 (3)	C9—N6—C8—N5	0.2 (4)
N4—C7—C8—N5	16.7 (3)	C9—N6—C8—C7	−177.0 (2)
N4—C7—C8—N6	−165.86 (19)	C9—C10—C11—N5	0.6 (4)
N4—C12—C13—C14	179.48 (19)	C11—N5—C8—N6	0.8 (4)
N4—C12—C17—C16	179.98 (18)	C11—N5—C8—C7	178.0 (2)
N6—C9—C10—C11	0.5 (5)	C12—N4—C6—N2	166.09 (19)
C1—N1—C5—C4	−0.4 (4)	C12—N4—C6—C5	−15.1 (3)
C1—N1—C5—C6	−178.2 (2)	C12—N4—C7—N3	−166.18 (18)
C1—C2—C3—C4	−1.7 (5)	C12—N4—C7—C8	18.9 (3)
C2—C3—C4—C5	1.1 (4)	C12—C13—C14—C15	1.0 (3)
C3—C4—C5—N1	0.0 (4)	C13—C12—C17—C16	−0.1 (3)
C3—C4—C5—C6	177.7 (2)	C13—C14—C15—F1	178.62 (19)
C4—C5—C6—N2	−32.5 (3)	C13—C14—C15—C16	−1.0 (4)
C4—C5—C6—N4	148.8 (2)	C14—C15—C16—C17	0.5 (4)
C5—N1—C1—C2	−0.2 (5)	C15—C16—C17—C12	0.1 (3)
C6—N2—N3—C7	−0.4 (2)	C17—C12—C13—C14	−0.4 (3)
C6—N4—C7—N3	−0.2 (2)

4-(4-Methylphenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L2_auto)

Crystal data

C18H14N6	Dx = 1.279 Mg m^−3
Mr = 314.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3494 reflections
a = 15.7069 (10) Å	θ = 2.5–29.1°
b = 11.8266 (11) Å	µ = 0.08 mm^−1
c = 17.5763 (12) Å	T = 293 K
V = 3265.0 (4) Å^3	Block, colourless
Z = 8	0.17 × 0.16 × 0.15 mm
F(000) = 1312

Data collection

Rigaku XtaLAB Synergy-R DW diffractometer with a HyPix detector	1901 reflections with I > 2σ(I)
ω scans	Rint = 0.116
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	θmax = 25.1°, θmin = 2.3°
Tmin = 0.986, Tmax = 0.988	h = −18→17
13041 measured reflections	k = −14→12
2885 independent reflections	l = −19→20

Refinement

Refinement on F^2	84 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0911P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
2885 reflections	Δρmax = 0.17 e Å^−3
264 parameters	Δρmin = −0.24 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.7327 (6)	0.7143 (9)	0.7364 (6)	0.072 (2)	0.463 (15)
N1A	0.7685 (8)	0.5238 (10)	0.6743 (9)	0.077 (3)	0.537 (15)
N2	0.57795 (11)	0.6717 (2)	0.66033 (10)	0.0738 (6)
N3	0.52512 (11)	0.67512 (19)	0.59781 (10)	0.0689 (6)
N4	0.65335 (8)	0.63004 (14)	0.55907 (9)	0.0446 (4)
N5	0.59188 (11)	0.69239 (18)	0.40577 (10)	0.0651 (5)
N6	0.45851 (10)	0.62154 (16)	0.44943 (11)	0.0613 (5)
C1	0.7947 (7)	0.7092 (12)	0.7837 (6)	0.092 (3)	0.463 (15)
H1	0.799769	0.765967	0.819973	0.110*	0.463 (15)
C1A	0.8367 (6)	0.4992 (8)	0.7145 (6)	0.078 (2)	0.537 (15)
H1A	0.865411	0.431957	0.704875	0.094*	0.537 (15)
C2	0.8541 (6)	0.6240 (15)	0.7834 (5)	0.086 (3)	0.463 (15)
H2	0.897391	0.622952	0.819459	0.103*	0.463 (15)
C2A	0.8672 (5)	0.5713 (8)	0.7713 (5)	0.069 (2)	0.537 (15)
H2A	0.914895	0.552054	0.799861	0.083*	0.537 (15)
C3	0.8491 (6)	0.5408 (14)	0.7296 (7)	0.090 (3)	0.463 (15)
H3	0.889682	0.483550	0.727983	0.108*	0.463 (15)
C3A	0.8251 (6)	0.6708 (7)	0.7839 (4)	0.0682 (19)	0.537 (15)
H3A	0.842542	0.720597	0.821815	0.082*	0.537 (15)
C4	0.7824 (10)	0.5426 (15)	0.6771 (11)	0.076 (3)	0.463 (15)
H4	0.776377	0.488276	0.639198	0.091*	0.463 (15)
C4A	0.7561 (7)	0.6946 (10)	0.7387 (7)	0.0680 (18)	0.537 (15)
H4A	0.727409	0.762402	0.746512	0.082*	0.537 (15)
C5	0.72861 (13)	0.6272 (2)	0.68533 (12)	0.0612 (6)
C6	0.65382 (12)	0.64461 (19)	0.63607 (11)	0.0556 (6)
C7	0.57106 (11)	0.65062 (17)	0.53805 (11)	0.0486 (5)
C8	0.53903 (11)	0.65312 (17)	0.45930 (11)	0.0461 (5)
C9	0.43020 (15)	0.6304 (2)	0.37810 (16)	0.0722 (7)
H9	0.374351	0.608988	0.368030	0.087*
C10	0.47852 (18)	0.6690 (2)	0.31916 (14)	0.0767 (8)
H10	0.456760	0.673876	0.270055	0.092*
C11	0.56022 (17)	0.7002 (2)	0.33530 (13)	0.0740 (7)
H11	0.594684	0.727501	0.296399	0.089*
C12	0.72520 (10)	0.59963 (16)	0.51216 (11)	0.0429 (5)
C13	0.72638 (11)	0.49870 (19)	0.47468 (13)	0.0547 (5)
H13	0.679812	0.450259	0.477123	0.066*
C14	0.79750 (13)	0.4693 (2)	0.43310 (14)	0.0672 (7)
H14	0.798442	0.400489	0.407559	0.081*
C15	0.86783 (12)	0.5404 (2)	0.42854 (13)	0.0604 (6)
C16	0.86363 (12)	0.6421 (2)	0.46576 (14)	0.0623 (6)
H16	0.909371	0.691848	0.462664	0.075*
C17	0.79330 (12)	0.67211 (19)	0.50752 (12)	0.0539 (5)
H17	0.791778	0.741324	0.532589	0.065*
C18	0.94599 (16)	0.5079 (3)	0.38356 (19)	0.0980 (10)
H18A	0.981640	0.573071	0.376907	0.147*
H18B	0.929106	0.479457	0.334676	0.147*
H18C	0.976901	0.450441	0.410504	0.147*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.061 (4)	0.107 (5)	0.047 (3)	0.001 (3)	−0.008 (3)	−0.016 (3)
N1A	0.063 (5)	0.093 (3)	0.074 (4)	0.008 (3)	−0.021 (4)	−0.004 (3)
N2	0.0595 (11)	0.1190 (18)	0.0427 (10)	0.0293 (10)	0.0036 (9)	−0.0048 (10)
N3	0.0510 (10)	0.1107 (17)	0.0448 (10)	0.0258 (9)	0.0043 (8)	−0.0004 (9)
N4	0.0369 (8)	0.0571 (11)	0.0398 (9)	0.0040 (6)	0.0037 (7)	−0.0016 (7)
N5	0.0602 (10)	0.0851 (15)	0.0499 (11)	−0.0041 (9)	0.0047 (9)	0.0098 (9)
N6	0.0437 (9)	0.0784 (14)	0.0620 (12)	0.0004 (8)	−0.0043 (9)	0.0012 (9)
C1	0.068 (5)	0.140 (7)	0.067 (4)	−0.003 (4)	−0.015 (4)	0.005 (5)
C1A	0.069 (3)	0.088 (4)	0.077 (4)	0.000 (3)	−0.027 (3)	−0.002 (3)
C2	0.058 (4)	0.141 (9)	0.058 (4)	0.004 (5)	−0.013 (4)	0.018 (6)
C2A	0.054 (3)	0.091 (4)	0.063 (4)	−0.002 (3)	−0.013 (3)	0.001 (3)
C3	0.058 (4)	0.142 (8)	0.070 (5)	0.004 (5)	−0.017 (4)	0.019 (6)
C3A	0.063 (4)	0.091 (4)	0.051 (3)	0.000 (3)	−0.011 (3)	0.003 (3)
C4	0.045 (4)	0.117 (6)	0.065 (6)	0.019 (5)	−0.008 (4)	0.021 (5)
C4A	0.062 (4)	0.096 (4)	0.045 (3)	0.009 (3)	−0.008 (3)	−0.004 (2)
C5	0.0477 (11)	0.0935 (16)	0.0425 (11)	−0.0015 (10)	0.0007 (9)	0.0019 (10)
C6	0.0502 (11)	0.0748 (15)	0.0416 (11)	0.0082 (9)	0.0007 (9)	−0.0048 (9)
C7	0.0368 (9)	0.0627 (13)	0.0461 (11)	0.0095 (8)	0.0046 (8)	0.0014 (9)
C8	0.0392 (9)	0.0541 (12)	0.0450 (11)	0.0058 (7)	0.0020 (8)	0.0023 (8)
C9	0.0571 (13)	0.0838 (18)	0.0756 (17)	0.0076 (11)	−0.0186 (13)	−0.0107 (13)
C10	0.0930 (19)	0.090 (2)	0.0466 (13)	0.0229 (14)	−0.0167 (13)	−0.0050 (12)
C11	0.0839 (17)	0.091 (2)	0.0475 (13)	0.0027 (13)	0.0076 (13)	0.0108 (12)
C12	0.0341 (8)	0.0530 (12)	0.0416 (10)	0.0002 (7)	0.0034 (8)	0.0010 (8)
C13	0.0405 (10)	0.0586 (13)	0.0648 (13)	−0.0064 (8)	0.0083 (10)	−0.0091 (10)
C14	0.0545 (11)	0.0686 (16)	0.0786 (17)	−0.0034 (10)	0.0156 (12)	−0.0217 (12)
C15	0.0438 (10)	0.0756 (17)	0.0618 (14)	0.0020 (9)	0.0145 (10)	−0.0028 (11)
C16	0.0418 (10)	0.0722 (16)	0.0730 (16)	−0.0125 (9)	0.0089 (10)	0.0013 (12)
C17	0.0465 (10)	0.0546 (13)	0.0605 (14)	−0.0068 (8)	0.0048 (10)	−0.0068 (10)
C18	0.0659 (15)	0.120 (3)	0.108 (2)	0.0026 (15)	0.0404 (16)	−0.0081 (18)

Geometric parameters (Å, º)

N1—C1	1.283 (10)	C4—H4	0.9300
N1—C5	1.368 (10)	C4—C5	1.317 (14)
N1A—C1A	1.316 (11)	C4A—H4A	0.9300
N1A—C5	1.387 (11)	C4A—C5	1.304 (11)
N2—N3	1.377 (2)	C5—C6	1.474 (3)
N2—C6	1.306 (2)	C7—C8	1.473 (3)
N3—C7	1.307 (2)	C9—H9	0.9300
N4—C6	1.364 (2)	C9—C10	1.363 (4)
N4—C7	1.366 (2)	C10—H10	0.9300
N4—C12	1.443 (2)	C10—C11	1.365 (4)
N5—C8	1.338 (2)	C11—H11	0.9300
N5—C11	1.338 (3)	C12—C13	1.364 (3)
N6—C8	1.330 (2)	C12—C17	1.373 (3)
N6—C9	1.334 (3)	C13—H13	0.9300
C1—H1	0.9300	C13—C14	1.379 (3)
C1—C2	1.373 (11)	C14—H14	0.9300
C1A—H1A	0.9300	C14—C15	1.390 (3)
C1A—C2A	1.397 (9)	C15—C16	1.371 (3)
C2—H2	0.9300	C15—C18	1.510 (3)
C2—C3	1.367 (11)	C16—H16	0.9300
C2A—H2A	0.9300	C16—C17	1.373 (3)
C2A—C3A	1.369 (9)	C17—H17	0.9300
C3—H3	0.9300	C18—H18A	0.9600
C3—C4	1.397 (13)	C18—H18B	0.9600
C3A—H3A	0.9300	C18—H18C	0.9600
C3A—C4A	1.373 (10)
C1—N1—C5	115.1 (7)	N4—C6—C5	124.72 (17)
C1A—N1A—C5	119.2 (9)	N3—C7—N4	110.15 (17)
C6—N2—N3	107.25 (17)	N3—C7—C8	124.22 (16)
C7—N3—N2	107.59 (16)	N4—C7—C8	125.51 (16)
C6—N4—C7	104.54 (15)	N5—C8—C7	117.12 (16)
C6—N4—C12	126.43 (14)	N6—C8—N5	126.56 (18)
C7—N4—C12	129.03 (16)	N6—C8—C7	116.21 (17)
C11—N5—C8	116.38 (19)	N6—C9—H9	118.1
C8—N6—C9	114.7 (2)	N6—C9—C10	123.7 (2)
N1—C1—H1	118.3	C10—C9—H9	118.1
N1—C1—C2	123.3 (9)	C9—C10—H10	121.4
C2—C1—H1	118.3	C9—C10—C11	117.1 (2)
N1A—C1A—H1A	119.1	C11—C10—H10	121.4
N1A—C1A—C2A	121.9 (9)	N5—C11—C10	121.6 (2)
C2A—C1A—H1A	119.1	N5—C11—H11	119.2
C1—C2—H2	120.3	C10—C11—H11	119.2
C3—C2—C1	119.5 (8)	C13—C12—N4	120.32 (15)
C3—C2—H2	120.3	C13—C12—C17	120.47 (17)
C1A—C2A—H2A	120.8	C17—C12—N4	119.18 (17)
C3A—C2A—C1A	118.4 (8)	C12—C13—H13	120.4
C3A—C2A—H2A	120.8	C12—C13—C14	119.16 (18)
C2—C3—H3	120.4	C14—C13—H13	120.4
C2—C3—C4	119.3 (10)	C13—C14—H14	119.3
C4—C3—H3	120.4	C13—C14—C15	121.5 (2)
C2A—C3A—H3A	121.2	C15—C14—H14	119.3
C2A—C3A—C4A	117.6 (8)	C14—C15—C18	121.5 (2)
C4A—C3A—H3A	121.2	C16—C15—C14	117.70 (19)
C3—C4—H4	122.6	C16—C15—C18	120.8 (2)
C5—C4—C3	114.8 (12)	C15—C16—H16	119.3
C5—C4—H4	122.6	C15—C16—C17	121.36 (19)
C3A—C4A—H4A	118.2	C17—C16—H16	119.3
C5—C4A—C3A	123.5 (8)	C12—C17—H17	120.1
C5—C4A—H4A	118.2	C16—C17—C12	119.8 (2)
N1—C5—C6	108.5 (4)	C16—C17—H17	120.1
N1A—C5—C6	113.6 (5)	C15—C18—H18A	109.5
C4—C5—N1	127.9 (7)	C15—C18—H18B	109.5
C4—C5—C6	123.5 (7)	C15—C18—H18C	109.5
C4A—C5—N1A	119.3 (6)	H18A—C18—H18B	109.5
C4A—C5—C6	126.9 (4)	H18A—C18—H18C	109.5
N2—C6—N4	110.48 (17)	H18B—C18—H18C	109.5
N2—C6—C5	124.75 (19)
N1—C1—C2—C3	1.3 (15)	C4A—C5—C6—N4	133.2 (7)
N1—C5—C6—N2	−46.4 (7)	C5—N1—C1—C2	0.9 (14)
N1—C5—C6—N4	136.5 (6)	C5—N1A—C1A—C2A	4.0 (18)
N1A—C1A—C2A—C3A	−1.1 (14)	C6—N2—N3—C7	−0.4 (3)
N1A—C5—C6—N2	126.3 (8)	C6—N4—C7—N3	−0.3 (2)
N1A—C5—C6—N4	−50.9 (8)	C6—N4—C7—C8	175.63 (19)
N2—N3—C7—N4	0.4 (3)	C6—N4—C12—C13	114.7 (2)
N2—N3—C7—C8	−175.6 (2)	C6—N4—C12—C17	−63.5 (3)
N3—N2—C6—N4	0.2 (3)	C7—N4—C6—N2	0.1 (2)
N3—N2—C6—C5	−177.3 (2)	C7—N4—C6—C5	177.6 (2)
N3—C7—C8—N5	141.3 (2)	C7—N4—C12—C13	−65.3 (3)
N3—C7—C8—N6	−35.2 (3)	C7—N4—C12—C17	116.5 (2)
N4—C7—C8—N5	−34.1 (3)	C8—N5—C11—C10	−0.4 (4)
N4—C7—C8—N6	149.4 (2)	C8—N6—C9—C10	−0.3 (3)
N4—C12—C13—C14	−176.98 (19)	C9—N6—C8—N5	0.5 (3)
N4—C12—C17—C16	177.20 (19)	C9—N6—C8—C7	176.68 (18)
N6—C9—C10—C11	−0.2 (4)	C9—C10—C11—N5	0.5 (4)
C1—N1—C5—C4	−3.3 (19)	C11—N5—C8—N6	−0.2 (3)
C1—N1—C5—C6	179.3 (8)	C11—N5—C8—C7	−176.3 (2)
C1—C2—C3—C4	−1.5 (17)	C12—N4—C6—N2	−179.9 (2)
C1A—N1A—C5—C4A	−4.5 (18)	C12—N4—C6—C5	−2.4 (3)
C1A—N1A—C5—C6	179.2 (10)	C12—N4—C7—N3	179.67 (19)
C1A—C2A—C3A—C4A	−1.2 (13)	C12—N4—C7—C8	−4.4 (3)
C2—C3—C4—C5	0 (2)	C12—C13—C14—C15	−0.1 (4)
C2A—C3A—C4A—C5	0.6 (16)	C13—C12—C17—C16	−1.0 (3)
C3—C4—C5—N1	3 (2)	C13—C14—C15—C16	−1.2 (4)
C3—C4—C5—C6	−179.9 (9)	C13—C14—C15—C18	179.5 (2)
C3A—C4A—C5—N1A	2.2 (16)	C14—C15—C16—C17	1.4 (4)
C3A—C4A—C5—C6	177.9 (7)	C15—C16—C17—C12	−0.3 (4)
C4—C5—C6—N2	136.0 (12)	C17—C12—C13—C14	1.2 (3)
C4—C5—C6—N4	−41.1 (12)	C18—C15—C16—C17	−179.3 (2)
C4A—C5—C6—N2	−49.6 (8)